503-17-3

Usage

Uses

Used in Organic Synthesis:
2-Butyne is used as a building block for a wide variety of chemicals due to its versatile carbon-carbon triple bond, which allows for various chemical reactions and transformations.
Used in Chemical Production:
2-Butyne is used as a raw material in the production of polymers and elastomers, contributing to the development of materials with specific properties for different applications.
Used in Industrial Applications:
2-Butyne is used as a precursor in the synthesis of various industrial chemicals, highlighting its importance in the chemical industry.
Safety Consideration:
2-Butyne is highly flammable, and extreme caution should be taken while handling 2-Butyne to prevent accidents and ensure safe usage in various applications.

InChI:InChI=1/C4H6/c1-3-4-2/h1-2H3

Upstream product

• 106-98-9 1-butylene 
• 107-01-7 butene-2 
• 107-00-6 but-1-yne 
• 5408-86-6 2,3-dibromobutane 
• 590-19-2 2,3-dimethylbutene 
• 13294-71-8 2-bromo-but-2-ene 
• 543-80-6 barium(II) acetate 
• 56-23-5 tetrachloromethane 
• 1066-26-8 sodium acetylide 
• 77-78-1 dimethyl sulfate 
• 627-41-8 propargyl alcohol methyl ether 
• 21134-90-7 5,6-dimethyl-1,2,4-triazine 
• 109-72-8 n-butyllithium 
• 513-37-1 2-methylprop-1-enyl chloride 

Downstream Products

• 676-80-2 methane-d3 
• 91345-39-0 2-p-tolylsulfanyl-but-2t-ene 
• 87-85-4 Hexamethylbenzene 
• 107-00-6 but-1-yne 
• 590-19-2 2,3-dimethylbutene 
• 590-18-1 (Z)-2-Butene 
• 598-71-0 DL-2,3-dibromobutane 
• 50341-35-0 2,2-dibromobutane 
• 3017-68-3 (Z)-2-Bromo-2-butene 
• 19398-48-2 2,3-dibromo-but-2-ene 
• 353-81-1 2,2-difluorobutane 
• 2648-57-9 3,3-Dichloro-2-butanone 
• 487-52-5 3,4,2',4'-tetrahydroxy-chalcone 
• 1194-30-5 trans-3,4-dichloro-1,2,3,4-tetramethylcyclobutene 

Relevant academic research and scientific papers

Development of a well-defined silica-supported tungstenocarbyne complex as efficient heterogeneous catalyst for alkyne metathesis

The interaction of [W({triple bond, long}C-tBu)(CH2-tBu)(OAr)2] (Ar = 2,6-iPr2C6H3) (1), with the hydroxyl groups of a silica dehydroxylated at 700 °C leads to [({triple bond, long}SiO)W(OAr)2({triple bond, long}C-tBu)] (2) which was characterized by IR, solid-state NMR and mass balance analysis. This well-defined surface species is an efficient catalyst for the metathesis of pent-2-yne.

REACTIONS OF DIMETHYLSELENADIAZOLE AND ALKYLTIN DERIVATIVES

Reactions of 4,5-dimethyl-1,2,3-selenadiazole with hexaalkylditins or trialkyltin anion followed by quenching with trialkyltin chloride affords only dimethylacetylene and bis(trimethyltin) selenide.Implications of these results in relation to possible syntheses of selenatellurafulvalenes are discussed.

Use of but-1-yne as a probe for the characterization of the basicity of alkali-exchanged zeolites

But-1-yne has been adsorbed at room temperature on a series of LiNa, Na and CsNaX and Y zeolites and also on CsNaX,9Cs and CsNaY,9Cs samples containing nine Cs atoms occluded by a unit cell. An IR study of the 3000-2800 cm-1 frequency range clearly showed that but-1-yne isomerized into but-2-yne on CsNaX,9Cs whereas the observation of a band near 1950 cm-1 in the case of CsNaY,9Cs characterized the formation of buta-1,2-diene. Such partial transformation of but-1-yne to isomers did not occur on LiNa and Na samples, allowing one to study the basicity of such zeolites from the v(≡CH) shift which decreases in the following order: NaX > LiNaX > NaY > LiNaY. The main feature is the observation of at least two perturbed v(≡CH) bands for the NaX and NaY samples, revealing the heterogeneity of the basic sites. This result is discussed taking into account the presence of cations in different positions.

Quantifying Error Correction through a Rule-Based Model of Strand Escape from an [ n]-Rung Ladder

The rational design of 3D structures (MOFs, COFs, etc.) is presently limited by our understanding of how the molecular constituents assemble. The common approach of using reversible interactions (covalent or noncovalent) becomes challenging, especially when the target is made from multivalent building blocks and/or under conditions of slow exchange, as kinetic traps and nonequilibrium product distributions are possible. Modeling the time course of the assembly process is difficult because the reaction networks include many possible pathways and intermediates. Here we show that rule-based kinetic simulations efficiently model dynamic reactions involving multivalent building blocks. We studied "strand escape from an [n]-rung ladder" as an example of a dynamic process characterized by a complex reaction network. The strand escape problem is important in that it predicts the time a dynamic system needs to backtrack from errors involving [n]-misconnections. We quantify the time needed for error correction as a function of the dissociation rate coefficient, strand valency, and seed species. We discuss the simulation results in relation to a simple probabilistic framework that captures the power law dependence on the strand's valency, and the inverse relationship to the rung-opening rate coefficient. The model also tests the synthetic utility of a one-rung (i.e., hairpin) seed species, which, at intermediate times, bifurcates to a long-lived, fully formed [n]-rung ladder and a pair of separated strands. Rule-based models thus give guidance to the planning of a dynamic covalent synthesis by predicting time to maximum yield of persistent intermediates for a particular set of rate coefficients and valency.

"canopy Catalysts" for Alkyne Metathesis: Molybdenum Alkylidyne Complexes with a Tripodal Ligand Framework

A new family of structurally well-defined molybdenum alkylidyne catalysts for alkyne metathesis, which is distinguished by a tripodal trisilanolate ligand architecture, is presented. Complexes of type 1 combine the virtues of previous generations of silanolate-based catalysts with a significantly improved functional group tolerance. They are easy to prepare on scale; the modularity of the ligand synthesis allows the steric and electronic properties to be fine-tuned and hence the application profile of the catalysts to be optimized. This opportunity is manifested in the development of catalyst 1f, which is as reactive as the best ancestors but exhibits an unrivaled scope. The new catalysts work well in the presence of unprotected alcohols and various other protic groups. The chelate effect entails even a certain stability toward water, which marks a big leap forward in metal alkylidyne chemistry in general. At the same time, they tolerate many donor sites, including basic nitrogen and numerous heterocycles. This aspect is substantiated by applications to polyfunctional (natural) products. A combined spectroscopic, crystallographic, and computational study provides insights into structure and electronic character of complexes of type 1. Particularly informative are a density functional theory (DFT)-based chemical shift tensor analysis of the alkylidyne carbon atom and 95Mo NMR spectroscopy; this analytical tool had been rarely used in organometallic chemistry before but turns out to be a sensitive probe that deserves more attention. The data show that the podand ligands render a Mo-alkylidyne a priori more electrophilic than analogous monodentate triarylsilanols; proper ligand tuning, however, allows the Lewis acidity as well as the steric demand about the central atom to be adjusted to the point that excellent performance of the catalyst is ensured.

Molybdenum Alkylidyne Complexes with Tripodal Silanolate Ligands: The Next Generation of Alkyne Metathesis Catalysts

A new type of molybdenum alkylidyne catalysts for alkyne metathesis is described, which is distinguished by an unconventional podand topology. These structurally well-defined complexes are easy to make on scale and proved to be tolerant toward numerous functional groups; even certain protic substituents were found to be compatible. The new catalysts were characterized by X-ray crystallography and by spectroscopic means, including 95Mo NMR.

Molecular and Silica-Supported Molybdenum Alkyne Metathesis Catalysts: Influence of Electronics and Dynamics on Activity Revealed by Kinetics, Solid-State NMR, and Chemical Shift Analysis

Molybdenum-based molecular alkylidyne complexes of the type [MesC≡Mo{OC(CH3)3-x(CF3)x}3] (MoF0, x = 0; MoF3, x = 1; MoF6, x = 2; MoF9, x = 3; Mes = 2,4,6-trimethylphenyl) and their silica-supported analogues are prepared and characterized at the molecular level, in particular by solid-state NMR, and their alkyne metathesis catalytic activity is evaluated. The 13C NMR chemical shift of the alkylidyne carbon increases with increasing number of fluorine atoms on the alkoxide ligands for both molecular and supported catalysts but with more shielded values for the supported complexes. The activity of these catalysts increases in the order MoF0 3 6 before sharply decreasing for MoF9, with a similar effect for the supported systems (MoF0 ≈ MoF9 6 3). This is consistent with the different kinetic behavior (zeroth order in alkyne for MoF9 derivatives instead of first order for the others) and the isolation of stable metallacyclobutadiene intermediates of MoF9 for both molecular and supported species. Detailed solid-state NMR analysis of molecular and silica-supported metal alkylidyne catalysts coupled with DFT/ZORA calculations rationalize the NMR spectroscopic signatures and discernible activity trends at the frontier orbital level: (1) increasing the number of fluorine atoms lowers the energy of the π?(M≡C) orbital, explaining the more deshielded chemical shift values; it also leads to an increased electrophilicity and higher reactivity for catalysts up to MoF6, prior to a sharp decrease in reactivity for MoF9 due to the formation of stable metallacyclobutadiene intermediates; (2) the silica-supported catalysts are less active than their molecular analogues because they are less electrophilic and dynamic, as revealed by their 13C NMR chemical shift tensors.

An acelylenically of a diene compound and/or method of manufacturing

Provided is a novel method for producing a compound having acetylene bonds and/or a diene. The method for producing a compound having acetylene bonds and/or a diene is characterized in that at least one selected from the group consisting of ketone compound (I), ketone compound (II), aldehyde compound (III), aldehyde compound (IV), and aldehyde compound (V) is dehydrated in the presence of a catalyst wherein a carrier containing silica supports at least one selected from the group consisting of compounds containing group 1 metal elements, compounds containing group 2 metal elements, group 1 metal elements, and group 2 metal elements.

Catalysts for the alkyne metathesis

Organometallic compounds of the general formula (I), in which M=Mo, W, are claimed.

The elusive ethenediselone, Se=C=C=Se

The neutral ethenediselone, Se=C=C=Se, has been characterised by neutralisation-reionisation mass spectrometry, which implies a minimum lifetime of the order of microseconds. Tetraselenafulvalene 1 and tetramethyltetraselenafulvalene 2 were used as precursor molecules. Flash vacuum thermolysis (FVT) of these compounds with isolation of the products in Ar matrices permitted the identification of ethyne, 2-butyne, CSe2, and selenoketene, H2C=C=Se, but at best traces of Se=C=C=Se survived the FVT/matrix isolation experiment. Multiconfigurational calculations indicate that Se=C=C=Se is a ground state triplet molecule with a very small singlet-triplet gap.